Abstract
Furylimino- and furfurylidenephosphoranes have been synthesized by sequential conversions of 5-unsubstituted and 5-methylfurfut),Iidetiedio.yanediones. The ylide fragment linked directly with the furfurylidenedioxanedione residue displays strong electron-donating properties, as a result of which resonance occurs in the system of conjugated bonds. The molecular and crystal structure of the iminophosphorane was studied by x-ray structural analysis and the resonance of the bonds in the molecule was confirmed.
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G. D. Krapivin, N. I. Val'ter, T. Ya. Kaklyugina, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 3, 327 (1994).
A. S. Tarasevich, I. E. Boldeskul, and V. P. Kukhar’, Usp. Khim.,55, 1344 (1986).
D. J. H. Smith, Comprehensive Organic Chemistry [Russian translation], Vol. 5, Khimiya, Moscow (1983), p. 96.
D. Vegh, J. Kovac, and M. Dandarova, Collect. Czech. Chem. Commun.,44, 1630 (1979).
I. N. Chernyuk, M. K. Bratenko, and M. I. Shevchuk, Zh. Obshch. Khim.,58, 306 (1988).
G. D. Krapivin, V. G. Kul'nevich, and N. I. Val'ter, Khim. Geterotsikl. Soedin., No. 10, 1325 (1986).
G. D. Krapivin, V. E. Zavodnik, N. I. Val'ter, V. K. Bel'skii, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 11, 1453 (1988).
G. D. Krapivin, V. G. Kul'nevich, and N. I. Val'ter, Khim. Geterotsikl. Soedin., No. 10, 1338 (1989).
D. W. Cruikshank, Acta Crystallog.,17, 671 (1964).
N. G. Bokii, Yu. T. Struchkov, A. E. Kalinin, V. G. Andrianov, and T. N. Sal'nikova, Progress in Science and Technology. Crystallochemistry [in Russian], Vol. 12, All-Union Institute of Scientific and Technical Information (VINITI), Moscow (1977), p. 56.
I. E. Mikhailov, O. E. Kompan, N. I. Makarova, A. I. Yanovskii, Yu. T. Struchkov, L. P. Oleklmovich, M. I. Knyazhevskii, and V. I. Minkin, Zh. Org. Khim.,21, 237 (1985).
G. M. Sheldrick, Computational Crystallography, Oxford University Press, New York (1982), p. 506.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 335–344, March, 1994.
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Krapivin, G.D., Val'ter, N.I., Zavodnik, V.E. et al. 5-[5-R-furfurylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones 6. Synthesis, structure, and properties of substituted furylimino- and furfurylidenephosphoranes. Molecular and crystal structure of N-[5-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl-2-furylimino(triphenyl)phosphorane. Chem Heterocycl Compd 30, 296–304 (1994). https://doi.org/10.1007/BF01165694
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DOI: https://doi.org/10.1007/BF01165694